One unit is already occupied and I'm working to get the other unit rented ASAP.

Every room occupied for sleeping purposes by one person shall contain at least seventy (70) square feet of habitable room area and every room occupied for sleeping purposes by two (2) people shall contain at least fifty (50) square feet of habitable room area for each person.

Must have multi-family zoning and be 500+ feet away from another non-owner occupied STR or you must live in the property for 6 months out of the year. 

It would just have to be non-owner-occupied and with a 20% done payment. 

Over the summer I used a VA loan to purchase a 3br/1b per unit duplex that I'm currently house-hacking, doing a live-in remodel on the second floor with the first floor totally updated and occupied with college students.

is it fully occupied? 

As long as it's fully occupied it should be doable even as a first timer. 

It does later say in the agreement that it is:"binding upon persons who own, lease, sublease, or occupy any parcel or portion thereof"The inclusion of which seems to imply that long term renting and/or subleasing would NOT be commercial use.I'm trying to figure out if I'm taking a significant risk buying this property for use as an STR.

@David RodriguezMTR - $4K per month occupied for 9 months = $36,000LTR - $3K per month occupied for 12 months = $36,000Occupancy is everything. 

Listing it “as is” with a $25k rehab concession can attract these buyers.Consider these options:List on investor-focused platforms like Roofstock or BiggerPockets or Facebook Marketplaces, where you’ll find buyers who appreciate tenant-occupied properties.Network with local investors or REI groups in your area to find someone looking for a turnkey rental with upside potential.Hire a real estate agent experienced in selling tenant-occupied properties, but adjust your pricing to cover commissions if needed.Make sure to highlight the stable tenants and ADU potential—those could be big selling points!